Elliott, who inherited his mother’s good looks, was named for her side of the family. Not surprisingly, Mittie and Aunt Anna, who lived with the family from 1857 until her marriage to James K. Gracie in 1866, doted on the charming, albeit troubled, lad. Plagued by frequent migraines as a child, Elliott embarked upon a world tour instead of following his older brother to Harvard. One sister, Corinne Roosevelt Robinson, noted that Elliott, “more naturally a social leader” played a key role in prodding TR to become more outgoing and engaging.

Elliott married Anna Rebecca Hall, the oldest daughter of Valentine and Mary Hall, on December 1, 1883. The couple’s children included Anna Eleanor, Elliott, Jr., and Hall. Though the marriage seemed promising, Elliott could never escape the shackles of alcoholism. His repeated failures at overcoming his addiction included a stint in a Michigan treatment center. Finally, Elliott’s oldest sibling, Anna (Bamie) Roosevelt, arranged for the family to seek help abroad. When Bamie joined the family in France, she realized that Elliott was not progressing in his treatment, largely because he ignored his doctor’s advice. Therefore, she accompanied Anna and the three children back to New York.

Sadly, Elliott’s wife, Anna, died in 1892. Tragedy struck again in 1893, when Elliott, Jr., died of diphtheria just shy of his fourth birthday. Branded “a maniac, morally no less mentally” by his brother Theodore, Elliott relocated to Abingdon, Virginia. There he found solace in alcohol and his mistress, Katy Mann, a union which produced Elliott Roosevelt Mann. Following Elliott’s death on August 14, 1894, TR’s harsh assessment of his brother softened. He later wrote that Elliott “was like some stricken, hunted creature” who was pursued by “the most terrible demons that ever entered a man’s body and soul.”

The surviving children, Anna Eleanor, the future wife of Franklin Delano Roosevelt, and Hall “Gracie,” lived in Tivoli, New York, with their maternal grandmother, Mary Ludlow Hall, who distanced them from their Oyster Bay Roosevelt relatives.